Sodium hydride → tert-butyl-4-[(1R,2R)-2-({[4-(methylsulfonyl)benzyl]oxy}methyl)cyclopropyl]piperidine-1-carboxylate

HRID 1468824ノート

反応式

HRID 1468824 の反応式
[CH3:1][S:2]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[H-].[Na+].[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([C@H:28]2[CH2:30][C@H:29]2[CH2:31]I)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>CN(C=O)C>[C:15]([O:19][C:20]([N:22]1[CH2:23][CH2:24][CH:25]([C@H:28]2[CH2:30][C@H:29]2[CH2:31][O:10][CH2:9][C:8]2[CH:11]=[CH:12][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=2)[CH2:26][CH2:27]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 3801026(4-Methanesulfonylphenyl)methanolHCID 86717780tert-butyl-4-[(1R,2R)-2-(iodomethyl)cyclopropyl]piperidine-1-carboxylate

生成物 1

HCID 86717779tert-butyl-4-[(1R,2R)-2-({[4-(methylsulfonyl)benzyl]oxy}methyl)cyclopropyl]piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

4-(Methylsulfonyl)benzyl alcohol (1.0 g, 5.4 mmol) was dissolved in DMF (12 mL), and sodium hydride (60 wt % dispersion in oil, 320 mg, 8 mmol) was added. The iodide from step A (2.35 g, 6.4 mmol) in DMF (12 mL) was added and the resulting solution was stirred at RT for 15 h. The solution was quenched with sat. NH4Cl, and EtOAc. The organic layer was washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated. The residue was purified via silica gel column chromatography (2/1 hexanes/EtOAc) which provided the title compound.

後処理

  1. customThe solution was quenched with sat. NH4Cl, and EtOAc
  2. washThe organic layer was washed with water and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified via silica gel column chromatography (2/1 hexanes/EtOAc) which

出典と根拠

ORDレコード
ord-8939a06517de45dd9a4270bc99e806fb
出典データセット
uspto-grants-2015_04
特許番号
US09006228B2

反応ノート

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